5-MeO-DMT
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| Other names | 5-Methoxy-N,N-dimethyltryptamine; 5-Methoxy-N,N-DMT; 5-MeO-DMT; 5-OMe-DMT; MDMT; O-Methylbufotenin; Mebufotenin; Methylbufotenin; N,N,O-Trimethylserotonin; CT-4334; BPL-002; BPL-003; LSR-1019 |
| Routes of administration | Inhalation, insufflation, sublingual, intramuscular, intravenous, oral (with an MAOI) |
| Drug class | Serotonergic psychedelic (hallucinogen) |
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| Bioavailability | Oral: inactive (without an MAOI) or weak |
| Metabolism | Oxidative deamination (MAO), O-demethylation (CYP2D6) |
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| Elimination half-life | Minutes (12–19 min in mice, 6–16 min in rats) |
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| ECHA InfoCard | 100.012.558 |
| Chemical and physical data | |
| Formula | C13H18N2O |
| Molar mass | 218.300 g·mol−1 |
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5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine), also known as O-methylbufotenin or mebufotenin (INN), is a naturally occurring psychedelic of the tryptamine family. It is found in a wide variety of plant species, and is also secreted by the glands of at least one toad species, the Colorado River toad. It may occur naturally in humans as well. Like its close relatives dimethyltryptamine (DMT) and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include five-methoxy, the power, bufo, and toad venom. The drug has been described as the most powerful psychedelic and, by journalist Michael Pollan, as the "Mount Everest of psychedelics".
Adverse effects of 5-MeO-DMT include sickness, vomiting, headache, chest pressure, fatigue, anxiety, fear, terror, confusion, paranoia, crying, loss of awareness and motor control, and reactivations. The drug acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT1A and 5-HT2A receptors, among others. However, 5-MeO-DMT differs from most other serotonergic psychedelics in having 100- to 1,000-fold higher affinity for the serotonin 5-HT1A receptor over the serotonin 5-HT2A receptor. In relation to this, 5-MeO-DMT has been described as an "atypical" psychedelic and as producing subjective effects notably distinct from those of DMT and other psychedelics, for instance having a relative lack of visual effects. Nonetheless, 5-MeO-DMT reliably produces mystical experiences in most people who take it. Like DMT, 5-MeO-DMT is only active non-orally and has a very rapid onset of action and short duration. However, 5-MeO-DMT is 4- to 20-fold more potent than DMT in humans.
5-MeO-DMT was first described by 1936, was first isolated from natural sources by 1959, and was first reported to be hallucinogenic by 1970. The use of 5-MeO-DMT-containing toad venom was first described in 1984. It is a controlled substance in some countries, for instance the United States, United Kingdom, Australia, and New Zealand. The drug is used recreationally and several deaths have been reported in association with its use. Use of 5-MeO-DMT is rare compared with other psychedelics, with only 0.003% of the United States general population having reported taking it in 2019 (compared to 8.5% for psilocybin). 5-MeO-DMT is being developed for potential use in medicine in the treatment of neuropsychiatric disorders such as depression.